Twister ring lubricant



I problem exists which'causes a great deal of lost pared simply by heatingthedesired pet Patented July 22, 1952 a Z,604,452

V STATE-S I a 7 1,604,452 5f" 1 TWISTEHRING LUBRICANT ma 1 J. l 'Morway; Clark Township; tuna;

County, and David W. Young, Roselle, {,J

,I assigno'rsto' Standard- Oil Development o n pan'y, a'corporation oi' Delaware 1" N Drawing. Application December 30,1195- Serial No. 203,794: j

6 Claims; (0;. zsznsnaf This invention relates to a lubricating grease the advantagebfnQtimodifyiiig t tex u'of composition having characteristics that'make it the petrolatum greatly while '.r'n0re' .thafi doubling especially desirable as a twister ring lubricant. its melting point. Inaddition, the. amino phenol More particularly, this invention relates to a imparts oxidatioriresistarice characteristics nd twister ring grease prepared by thickening a prevents darkening of the petrol'atum, This prea white petrolatum to a greasejfconsistency with vents.yarrijdiscolorati Ill and the formation or anN-acyl amino phenol. I 1

v i I unpleasant odors 1 In the artof textile manufacture, a lubricating in general, .the ention re PIE.-

time, that of twister ring lubrication. In the 10 with from 1.0%.to 1,010 %;',pref,erablyl3%, textile manufacturing step in which this problem by weightof a desired N -acyl ammo phenol t, a exists, the untwisted yarniis twisted andwound temperature of the melting athigh speeds upon sjpools inj preparation for usua11y3240 to .2'75 'Wh the weaving looms. ,In the twistingand winding phenol is completel r operation two or'more' yarns, or plies, are brought 15 cooled withoutia'git n nduponsolidifica on, together and twisted :into a single strand and the product is afsm hunctuous mate alljof 3 then wound on't he spool, or bobbin, which is excellent appearance T mounted on a 'spindle within a twister frame. The petrolatum ed intheformulati'onof the The bobbin stands vertically within a circular greases of invention may bev anyof thewhite metal ring'called a twister ring'rnountedon the petrolatums having melting. points. within the twister-frame. Riding upon thetwister ring and range of from 75 to .125 F, and ASTMtco'ntravelling freely on "its circumference-is the sistencies of from 200 to. 325 .JmmJ LO. QTh -pretraveler, a loopedfnietal'member made of steel, ferred embodiment of the invention contem, orbronz'e. In'thezprocess oftwisting and'wind plates, however, the use-of a whiteipetrolatum ing, two or moreyarnsor'plies' pass throughfthev having-a melting point yvithina; rangewcfjfrom loop of the travelerare" twisted by its rotational, 112 to 124.F.-with.an ASTM consistencyl oi from movement around-the twister ring, and are 240 to 290- mm./l0. If petrolatum's' of'greater wound on the-bobbin, rotating upon the spindle. consistencies are employed, it may be necessary The bobbin rotates at speeds in the neighborto blend with them aminor amount of a white hood or-7,000 R. P.-M. or more and 'theftraveler oil to obtain desired handling properties. moves-around the twister ring at'speeds almost The N-acyl aminoi-phenolused forethe prepaas great. The extremity-of the need'for lubriration of the greases-oi. invention have the gen-e eating of the twister ring is emphasized when one eral formula: considers-that the traveler, weighing onlyafraction of an ouncefjmay develop several pounds 1 of centrifugal force "at topspee ds."

Twister ringgreases have hitherto been prepared using asaba'se'a white 611 and as thickening agents 'e;f'n'iixture' of calcium'and sodium 9 v soaps. Thesegreases' have metwith 'consider- 40 wherein R is an alkyl roup'fcontaining from 14 able success' but are not perfectlysatisfactory in to 22 carbon atoms, preferably an alkylgroup all instancessince carefulfcontrol is necessary in non-benzenoid.;in nature; and. wherein'R' and their manufacture to obtain the exact degree of R" arehydrogen atoms or alkylzgroups containviscosity necessary for satisfactory lubrication. ing from 1 to 20 carbon atoms; r Y Ifthe grease is too viscousyit will be thrown The preferred embodimentxotthis "invention from thering, discoloringthe'yarmandresulting contemplates the use; of, compounds according to in affailure of lubrication causingi high traveler the formula above wherein R and R" are hydrowear-and high yarn tensions which increasesithe gen atoms, and 'wher'ein R ts "a straight chain breakage rate. A grease that'is too thinwill drip a p ic group c' a fiOm16-to 20 carbon and spatter, with identical results. i r atoms, that is, the N- acyl pg-amino phenols. Ex-

It has now been found that excellent twister 11 3 013 fthesflipljfrrld compound'sffllfe ring greases may 'be-"p'repai'ed bythickening a -p w p-amlno i hfifi fNf e lqylp-a nq white petrolatum with-an' N acyl amino phenol phenol, andN araQhidOyI p-arnino phenol, with containing from'l' i to zg'fcarb'on atoms'in the N- stearoy p-iamino phenol'beingespecially pre-' acylportion thereof, Thesenovel greases'have fer-red.

3 The alkylated N-acyl p-amino phenols exemplified by the formula above when R and R" are alkyl groups containing from 1 to 20, preferably 4 to 15, carbon atoms are also operable in this invention. Compounds such as N-n-valeryllamino-3-pentade'cyl phenol, 'N-n-propanoyll amino-8-pentadecyl phenol, N-n-pentanoyli amino-2,6-dietert.-butyl phenol, N-n-hexyllamino-Z-hexyl phenol are examples of the alkylated phenols operable.

If desired the amino phenols having the amino to oxidation. In this test, a sample of the grease group meta to the hydroxy group may beuused in practicing this invention. .1That'isthe N-acyl m-amino phenols, either alkylated or not, may be.

used as petrolatum thickeners.

The preparation of these N-acyl amino phenols is accomplished by simply admixing the desired acid or acid chloride with the desired amino phenol and heating the mixture under proper reaction .conditions. The, reaction proceeds smoothly splitting ofi water, or' hydrogen chloride,

giving the desired amino phenol as an end product. .It'may then bejfpurlfled by any of the methods known to the art. Themethodfor th'e preparation of an operable p-amino'phenol'istypifiedby the following:

One mol of peaminqphenol was placed ;in a

.glass round bottomed fiask'liitted with a reflux condenser with an 'azeotropic take off arm., Therewas added tothe flask one mol of stearic acidand about. 50 gmil'ofgxylene. Thex'ylene served as an entraining agent for the water formed during the course of the reaction. The

. flask was then heated to the xylene reflux temperature and kept at that temperature for about hours, or until the theoretical water (1 mol) had been removed. The contents of the flask was then emptied into an evaporating dish and heated on a steam bath until thelast trace of xylene was removed. .The product was then recrystallized from acetic acid and there resulted a colorless Nrstearoyl p-amino phenol (melting point 132 C.)

The following examples. are given to more explicitlypointoutthis invention, it being kept in mind that'theyare exemplaryonly and do not restrict in any way the inventive concept as set outlabove.

To 93% 'b'y weight ofaiwhite petrolatum having .a melting point of 110 F. and an ASTM V V penetration of 2'75 mm./ 10 there was added 2. 0%

by weight of N-stearoyl p-amino phenol, prepared by reacting with p amino phenol a come mercial stearic acid derived from tallow and containing palmitic acid. The temperature of the mixture was then raised with agitation to the 1 melting pointof the amino phenol, about 240 F. The mixture was then allowed to cool to room temperature without agitation, and there resulted a smooth unctuous grease composition of gen erally excellent appearance. The dropping point of this grease composition was 220 F. and the AJSTM penetration 2751mm./ 10.

'It'has been found that N -stearoyl p-amino phenol has excellent thickening properties, but little anti-oxidant 'efiect, while conversely, the N -lauroyl p-amino phenol has little thickening ability but impartsexcellent resistance to oxidation tothese grease compositions. In order to utilize these properties, twister ring lubricants were prepared in accordance with the procedure 7 deta led in Example I above employing mixtures 5- ound 7 due to'ithe oxidation of the sample. reported in Tablei'I, below;

.Table I 'TWrsTE'R RING GREASES 7 Drop ASTM N-H Test Thickener ping 5 33 mm./10 Drop u I 0F e :1 Petrolatummuz 106 V 275 2.07%li-Istearoyl1p-amino ph1enoli 240 275 70 .75 -s earoy p-amino p eno .25% N-lauroyl p-aminophenoLhu 232 275 1.5g, Ifil-stearoy} p-a'rnino p%en0% .1, 222 275 400+ 1.0 -stearoy p-aminop e110 ".1 1.0%; N-lauroyl p-amino phenol; l. 4 2.0% N-lauroyl p'amin'o phenol 200 275 400+ 1 30.11. 5. Lin 70 hrsg' I V l If it is desiredto make a more of the soap. 1; 'This results in an obvious economic advantage in the preparation-of these lubricants. In addition incases .where a white oil is'employed in combination with the petrolatum to modify and givethe desired consistency,

the N-acyl p-amino phenol, whether employed as the thickener alone orin combination with metal soap thickeners, prevents,to a large degree, ex uding of the oil in service or in storage. To summarize briefly, this invention relates to improved twister ring lubricants consisting of a white'petrolatum alone or in combination with a white oil, thickened to a greaser consistency With an N-acyl amino phenol. These greases have desirable. un orm consistences and excel: lent anti-oxidant characteristics. i

' -What is claimedis}:

-l-.{A; new and improved ring lubricant,

consisting essentiallyof a white .petrolatum containing dispersed therein from 1% -to-10% by Weight, based on the. weight of the total.compo-- sition, of an N-acyl p-amino phenol, thepacyl group of which atoms. ,2. 'A' new and improved twister ring lubricant consisting essentiallyofa white petrol'atum .containing' dispersed therein fromfll to 10% by weight, based on the weight of the total composition, ofan *N acyl pj-amino phenol, the 'acyl group of which contains '161to 20 carbon atoms. 3. 'A new and improved twister; ring. lubricant consisting essentiallyota white petrolatum con: taining dispersedtherein from 3 to 6% by weight, based on theweight ,of the total compositiom of an N-acyl p-aminoph enol, the acyl grou ie: which contains from 16 to" 20 carbon atoms.

higher melting prcd uct, a-minor amount of acommon grease making contains from'12 to 22 carbon 7 4. A new and improved twister ring lubricant consisting essentially of a white petrolatum having a melting point within a range of. from 75 to 120 F., containing dispersed therein from 3 to 6% by weight, based on the weight of the total composition, of an Nacyl p-amino phenol, the acyl group of which contains from 16 to 20 atoms per molecule.

5. A new and improved twister ring lubricant consisting essentially of a white petrolatum having a melting point within a range of from 112 to 124 F., containing dispersed therein from 3 to 6% by weight, based on the. weight of the total composition, of N-stearoyl p-amino phenol.

6. A new and improved twister ring lubricant 15 Number consisting essentially of a white petrolatum con- REFERENCES CITED I The following references are of record in the file of this patent:

UNITED STATES PATENTS Name Date 2,065,857 Hilliker Dec. 29, 1936 

1. A NEW AND IMPROVED TWISTER RING LUBRICANT CONSISTING ESSENTIALLY OF A WHITE PETROLATUM CONTAINING DISPERSED THEREIN FROM 1% TO 10% BY WEIGHT, BASED ON THE WEIGHT OF THE TOTAL COMPOSITION, OF AN N-ACYL P-AMINO PHENOL, THE ACYL GROUP OF WHICH CONTAINS FROM 12 TO 22 CARBON ATOMS. 